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High-throughput and Comprehensive Drug Surveillance Using Multisegment Injection-Capillary Electrophoresis-Mass Spectrometry

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'Upenamide: trials and tribulations.

William P Unsworth¹, Richard J K Taylor

¹Department of Chemistry, University of York, Heslington, York, YO10 5DD, UK. william.unsworth@york.ac.uk richard.taylor@york.ac.uk.

Organic & Biomolecular Chemistry

|September 24, 2013

Summary

This summary is machine-generated.

Synthetic chemists attempted the total synthesis of the complex macrocycle upenamide. Despite synthesizing proposed structures, neither matched the natural product, highlighting challenges in natural product synthesis.

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Area of Science:

Natural Product Synthesis
Organic Chemistry
Medicinal Chemistry

Background:

The complex macrocycle upenamide was isolated in 2000.
Its unique structure prompted significant synthetic chemistry efforts for total synthesis and structural verification.

Purpose of the Study:

To detail the progress made by various research groups in the total synthesis of upenamide.
To describe the evolution of synthetic routes and the development of new methodologies.
To compare synthesized structures with the natural product's spectroscopic data.

Main Methods:

Review of published synthetic strategies and methodologies.
Analysis of spectroscopic data for synthesized compounds and natural upenamide.
Comparative structural elucidation of proposed and natural upenamide.

Main Results:

Multiple research groups successfully synthesized proposed structures of upenamide.
Spectroscopic analysis revealed discrepancies between synthesized structures and the natural material.
The synthetic efforts led to the development of novel synthetic routes and methodologies.

Conclusions:

The total synthesis of upenamide presented significant challenges.
Neither of the initially proposed structures accurately represented the natural product.
The synthetic endeavors advanced the field of complex macrocycle synthesis and methodology development.